Guesthouse holiday rentals in Winter Park

Guesthouse in Thornton Park

A charming exterior of a cottage-style house is framed by lush greenery and well-kept landscaping. A friendly Golden Retriever stands on the front lawn, which features a mix of plants and decorative elements. A welcoming porch with seating is visible, inviting relaxation.

4.89 out of 5 average rating, 789 reviews

Thornton Park's Historic Guest House - private

Please, read my reviews so you know what to expect when staying at the Thornton Park Guest House! Jackson, our Golden Retriever, is the real Super Host! Come join us for a weekend getaway, work trip or just so you don’t have to drive home after a fun night! We welcome all to stay with us! Orlando has some amazing historic neighborhoods that most people don't know about! Here's a great spot that's only a few blocks to Lake Eola, located in one of the most beautiful neighborhoods in FL!

A quaint exterior view of a small house surrounded by lush greenery. The porch is framed by a railing and features a couple of chairs, while string lights add a charming touch. Colorful flowers bloom in the foreground, enhancing the serene atmosphere.

4.94 out of 5 average rating, 442 reviews

Garden House near Orlando's cultural hub

On a quiet cobblestone street, yet close to art and culture, more than 3 dozen restaurants in walking distance, Florida Hospital and family-friendly activities. You’ll love our place because of the location, the large bathroom with jacuzzi, the skylights, window seat, porch swing. It is nestled in our back yard surrounded by trees and has its own private entrance via a rustic walk way of pavers and stones. Couples, families, most anyone will find it charming. STR 1009942 (City registration)

Guesthouse in Lake Cherokee

A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.

4.98 out of 5 average rating, 120 reviews

1924 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

4.98 out of 5 average rating, 123 reviews

A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.

Guesthouse in Longwood

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the quiet backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from Interstate-4. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not had issues. Grab bars are in the bathroom.

The front porch features two wicker chairs with bright orange cushions, inviting relaxation. Potted plants and hanging baskets add greenery, while a gentle overhang provides shade. A pathway leads to the entrance and a nearby guest house, framed by well-maintained shrubs.

4.97 out of 5 average rating, 358 reviews

Oasis Garden Cottage -cozy, chic, near everything!

Our cozy cottage is located within minutes of some of the best areas, restaurants, bars, and attractions Orlando has to offer. Winter Park and College Park are 3-5 minute drives, Disney and Universal only 20 minutes, etc. The interior is chic and inviting, with a homey feel. Enjoy the fireplace, play some board games, soak in bath salts in the claw foot tub, curl up on the porch with a coffee and read one of our provided books— it’s so peaceful you’ll have a hard time leaving for the day!

The exterior of the two-story cottage is captured, showcasing a red and white color scheme with black shutters. Lush green landscaping and a well-maintained lawn surround the home, while a concrete driveway leads to a detached garage nearby. A white picket fence adds charm to the property.

4.91 out of 5 average rating, 187 reviews

8th Green Cottage - A relaxing oasis in the city

The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located 5 minutes from downtown. Sitting on the historic 1924 Dubsdread golf course. Enjoy the great views, pleasant and quiet neighborhood all with easy access to everything Orlando has to offer. Location is key when traveling and the 8th Green Cottage delivers! Disney, Universal, and Sea World all within a straight shot down I4. Free play Arcade with 3500 games included in spare bedroom Pets are welcome and stay Free.

A cozy studio suite is shown with warm wood accents. A small kitchenette is equipped with a microwave and refrigerator. A workspace with a blue desk and two chairs is visible. Bright green plants add a touch of nature, complemented by a vibrant area rug.

4.76 out of 5 average rating, 532 reviews

Private Cozy Cottage in heart of Orlando

Come stay at our Cozy quaint suite located in the historic downtown Lake Davis neighborhood with a 5 minute walk to a quiet neighborhood market, 1 mile walk to downtown Orlando with entertainment and the Downtown Farmers Market. Less than 30 minutes to the worlds greatest attractions Disney, Universal Studios, Sea World etc. The beach is a 1 hour drive. One car parking. The room is connected to a family home you’re able to hear guest next door. Not for parties . Please NO pets.

Guesthouse in Wadeview Park

A spacious bedroom features a large bed with white bedding and decorative pillows. Two soft bedside lamps illuminate the area, complemented by a cozy armchair and a decorative bench at the foot of the bed. Exposed brick wall accents the room.

4.98 out of 5 average rating, 120 reviews

The Cottage A Pet Friendly Guesthouse

Welcome to The Cottage! A pet friendly, super cute, and quiet studio apartment built in 2016, located above the detached garage behind my house. Pets always stay for free, and no additional cleaning fees are charged. Private self access is provided so you come and go as you please. The unit has a full kitchen, king sized bed, 4 pillows, 100% cotton sheets and coverlet. Laundry detergent and dish soap are provided. Trash is located on the west sideof the building.

A spacious living area is highlighted by a sleek, modern design featuring polished floors. A green couch and two accent chairs are arranged around a wooden coffee table. A dining table with ample seating is situated nearby, complemented by decorative wall art and soft lighting.

4.99 out of 5 average rating, 173 reviews

Luxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF

This luxury guesthouse (on the same property as our main house but they are completely separate) is a hidden oasis conveniently located in the middle of downtown Winter Park (Rollins College/Full Sail) and UCF. It's roughly 10 minutes to each. Close to 417 expressway (toll road) so you can easily get around to the other areas of Orlando. Note: The guesthouse is 35 minutes to Disney, 25 minutes to Universal Studios and 20 minutes to Orlando International Airport.

A charming arched bridge is framed by lush greenery and hanging Spanish moss. The surroundings are filled with trees and plants, creating a serene outdoor space that invites exploration.

4.93 out of 5 average rating, 181 reviews

Jefferson St. Cottage

This cottage is a unique free-standing detached dwelling in the heart of Lawsona Park in the Historic District in downtown Orlando. It sits behind the owner's main house in the back of the lot; privacy is not an issue. The cottage is loaded with all the amenities needed to enjoy your stay. We are close to highways to visit Universal, Disney World, Sea World any more attractions in central Florida. In addition, Uber is a very good option for transportation.

A light blue elevated guesthouse features a spacious deck with white railings overlooking a landscaped yard. A set of stairs leads up to the entrance, surrounded by greenery and large trees. The ground area includes outdoor seating, complementing the serene environment.

4.98 out of 5 average rating, 245 reviews

The Loft in College Park

The Loft is a private guesthouse located above our garage near Downtown Orlando and Ivanhoe Village. It is walking distance to multiple restaurants, bars and shops. Also close to I-4 and easy access to the attractions. The studio space offers a queen size bed as well as a queen size sleeper sofa in the living room area. Luxurious full size bathroom with walk in shower and rain shower head. Perfect get away for those looking to enjoy Orlando!

Guesthouse in Lake Eola Heights

A serene pool area features a vibrant red pool float resting in the clear water, surrounded by lush greenery. Comfortable outdoor seating is arranged near the pool, with large umbrellas providing shade. The backdrop showcases a charming pool house with multiple glass doors, inviting natural light.

5 out of 5 average rating, 268 reviews

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

Popular amenities for Winter Park guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Guesthouse in Lake Eola Heights

A bright and airy studio space is depicted, featuring a spacious bed with a light-colored blanket. A wooden tray sits on the bed with a drink. A TV is mounted on the wall opposite a casual seating area with a coffee table and a comfortable couch.

4.94 out of 5 average rating, 268 reviews

Bright + Modern Downtown Guesthouse near Lake Eola

Guesthouse in Winter Garden

A welcoming outdoor space is presented with two patterned armchairs and a wicker chair arranged around a glass-topped table. A decorative wall feature adds texture, while potted plants and a decorative heron enhance the tranquil atmosphere. Warm light filters through the area.

4.93 out of 5 average rating, 102 reviews

Blue Heron Bungalow

Superhost

A small outdoor seating area features two chairs with tropical-themed cushions and a metal table between them. A green decorative flower hangs on the wall, and the tiled floor reflects a light color. A door is positioned nearby, leading to the interior.

4.77 out of 5 average rating, 631 reviews

Little Studio, Small studio.

An open space features a cozy sleeping area with a patterned quilt atop a spacious bed. A glass dining table with two modern chairs is positioned in the foreground, accented by a decorative vase. Light-colored tile flooring enhances the room's brightness.

4.96 out of 5 average rating, 220 reviews

Welcome to The Blue House

4.95 out of 5 average rating, 201 reviews

A well-equipped kitchen is visible, featuring modern cabinetry and stainless steel appliances. A small dining table is positioned in the foreground, adorned with a vase of fresh flowers. The backsplash adds a touch of elegance, complementing the overall clean and bright design.

Guesthouse in Clermont

Modern efficiency ~ Great location

Guesthouse in Southern Oaks

A bright living area is presented with vaulted ceilings and hardwood floors. Comfortable seating is arranged around a central coffee table, with soft lighting provided by table lamps. Natural light filters through the windows, illuminating the decor and creating a welcoming atmosphere.

4.85 out of 5 average rating, 111 reviews

Historic lakefront guesthouse

Superhost

A pathway made of concrete stepping stones is lined with white gravel, leading to a charming entrance of a small building. The surrounding area features minimal landscaping with green plants and trees visible, and a wooden fence encloses the space.

Guesthouse in Kissimmee

4.79 out of 5 average rating, 111 reviews

Unit B Apt Relax House

A sleeping area features a full bed with a floral-patterned blanket, complemented by a decorative 'COZY' pillow. A wall-mounted shelf displays a plant and decorative items, while a ceiling fan provides air circulation. Soft lighting creates a calm ambiance.

4.77 out of 5 average rating, 116 reviews

Private full kitchen near Disney & Epic Universe!

Guesthouses with a patio

Guesthouse in Park Lake/Highland

A cozy living area is adorned with deep green walls, featuring a spacious bed with decorative pillows and a textured blanket. A television is mounted against the wall, accompanied by a wooden console. A light-colored sofa adds to the inviting atmosphere, complemented by woven wall art.

4.91 out of 5 average rating, 287 reviews

“The Clementine” Boho Home in Orlando’s Food Scene

A spacious studio contains a king-size bed with a light-colored quilt, flanked by two bedside lamps. A small refrigerator and kitchenette are visible in the corner, while a ceiling fan provides airflow. Windows are adorned with light curtains, allowing natural light into the room.

4.87 out of 5 average rating, 147 reviews

King-size Studio 4 min to Universal

Guesthouse in Lake Eola Heights

A bright living space features a comfortable sectional sofa adorned with decorative pillows, paired with a light-colored armchair. A wooden coffee table sits on a textured area rug, while a ceiling fan and pendant lighting add modern touches. The kitchen bar is equipped with high stools, enhancing the open layout.

5 out of 5 average rating, 84 reviews

Livingston Hideaway - 2 Blocks From Lake Eola

A modern pool house is featured, with large glass doors opening to a swimming pool. The exterior includes a tree emblem and a small seating area with a chair. Sun loungers are positioned near the pool, surrounded by lush grass and a wooden fence.

4.98 out of 5 average rating, 93 reviews

Amazing New Pool House!

5 out of 5 average rating, 103 reviews

An exterior view of the guesthouse displays a quaint two-story structure with a black garage and a welcoming front porch. Surrounding greenery provides a natural setting, enhancing the privacy of the location. The two upper windows are adorned with large curtains.

Guesthouse in Ocoee

NEW 1BRM Guesthouse | King Bed | Central Florida

A cozy studio apartment features a comfortable bed adorned with soft linens and decorative pillows. Natural light filters through sheer curtains, illuminating a stylish wall-mounted TV and a small dining area. A woven rug adds texture to the dark wooden floor.

4.99 out of 5 average rating, 82 reviews

Charming Studio for two, 13 min from MCO Airport

A cozy bedroom features a spacious bed with a deep green headboard and coordinating bedding. A tufted bench is positioned at the foot of the bed. Natural light enters through a window, illuminating a side table and a small seating area with a fan overhead.

4.91 out of 5 average rating, 32 reviews

Love Nest Studio nearby highways and Airport

Guesthouse in Audubon Park

5 out of 5 average rating, 10 reviews

The Cottage at Starlab

Guest house rentals with a washing machine and dryer

A cozy seating area features a patterned armchair and a sleek gray sofa. A TV mounted on the wall displays a tranquil beach scene. Light streams in through a window with blinds, illuminating the natural wood floor and woven area rug.

4.93 out of 5 average rating, 255 reviews

Bungalow Near Epic, Disney and Downtown Orlando

Guesthouse in Thornton Park

The bedroom features a spacious bed dressed in a dark grey coverlet, accented by light pillows. Natural light enters through a window draped with white blinds. A ceiling fan provides air circulation, while artwork and bedside tables enhance the decor.

4.96 out of 5 average rating, 582 reviews

Private Luxurious Apt. - Historic Downtown Orlando

Guesthouse in Deer Island

An outdoor patio area features a screened enclosure with a private swimming pool. Comfortable seating is arranged around the pool, and lush greenery surrounds the space, providing a serene environment. Potted plants add a touch of color, enhancing the tranquil setting.

4.95 out of 5 average rating, 131 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

4.99 out of 5 average rating, 144 reviews

Top 1% ABNB Villa Oasis w/ Botanical Courtyard

The living area features a soft mustard-yellow sofa complemented by two green accent chairs. A glass coffee table sits in front of the sofa, and a large flat-screen TV is mounted on the wall, above a decorative piece showcasing soothing colors.

4.95 out of 5 average rating, 161 reviews

The 𝕆𝕣𝕝𝕒𝕟𝕕𝕠 is the first step in the process.

A comfortable living area features a dark leather sofa, a wooden coffee table, and a dining table with chairs. Bright light filters in from the outdoor patio, revealing lush greenery and a seating area beyond the sliding glass doors adorned with a vibrant red umbrella.

4.96 out of 5 average rating, 459 reviews

The Coach House -2 bedroom/3 bath Orlando Getaway!